Sodium borohydride → HCID 58920620, compound

HRID 1365494Notes

Reaction equation

HRID 1365494 reaction equation
[BH4-].[Na+].[Cl:3][C:4]1[CH:5]=[CH:6][C:7]([C@@:10]([NH:29][C:30]([CH:32]2[CH2:36][CH2:35][C:34](=[O:37])[CH2:33]2)=[O:31])([C:18]2[CH:23]=[C:22]([C:24]([F:27])([F:26])[F:25])[CH:21]=[C:20]([F:28])[CH:19]=2)[CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[N:8][CH:9]=1>C1COCC1.O>[Cl:3][C:4]1[CH:5]=[CH:6][C:7]([C@@:10]([NH:29][C:30]([CH:32]2[CH2:36][CH2:35][CH:34]([OH:37])[CH2:33]2)=[O:31])([C:18]2[CH:23]=[C:22]([C:24]([F:25])([F:26])[F:27])[CH:21]=[C:20]([F:28])[CH:19]=2)[CH2:11][C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)=[N:8][CH:9]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 58920434HCID 58920434, compound

Product 1

HCID 58920620HCID 58920620, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

NaBH4 (600 μg, 0.015 mmol) was added to a solution of N-((S)-1-(5-chloropyridin-2-yl)-1-(3-fluoro-5-(trifluoromethyl)phenyl)-2-phenylethyl)-3-oxocyclopentanecarboxamide (prepared as described in Example 7, Procedure 12) (7.7 mg, 0.015 mmol) in THF (1 mL) at room temperature. The reaction was monitored by HPLC and after 16 h, the solution was diluted with H2O and extracted with EtOAc (3×). The combined EtOAc layers was further washed with 6N HCl and sat'd aqueous NaCl, dried over Na2SO4, filtered, and concentrated under reduced pressure. Flash chromatography (SiO2, 0-100% EtOAc/hexanes) gave 5.4 mg of N-((S)-1-(5-chloropyridin-2-yl)-1-(3-fluoro-5-(trifluoromethyl)phenyl)-2-phenylethyl)-3-hydroxycyclopentanecarboxamide as a film. 1H NMR (500 MHz, CDCl3, mixture of isomers) δ 8.54 (s, 1H), 8.52 (s, 1H), 8.35-8.29 (m, 2H), 7.72-7.66 (m, 2H), 7.47-7.42 (m, 2H), 7.40-7.32 (m, 2H), 7.25-7.06 (m, 10H), 6.56-6.50 (m, 4H), 4.48-4.38 (m, 2H), 4.30-4.22 (m, 2H), 3.64-3.53 (m, 2H), 2.89-2.80 (m, 2H), 2.10-0.80 (m, 12H); LC/MS (MeOH/H2O/NH4OAc mobile phase) rt=3.91 min; [M+H]=507.3.

Workup

  1. extractionextracted with EtOAc (3×)
  2. washThe combined EtOAc layers was further washed with 6N HCl
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b106de6b2c094a51bc5a1ad20b8ca648
Source dataset
uspto-grants-2011_02
Patent number
US07888376B2

Reaction notes

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